Potassium Hydroxide → HCID 22013056, compound

HRID 378712Notes

Reaction equation

HRID 378712 reaction equation
C([O:3][C:4]([CH2:6][C:7]1([NH:17][C:18]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16])=[O:5])C.[OH-].[K+]>C(O)C>[OH:5][C:4]([CH2:6][C:7]1([NH:17][C:18]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22012986HCID 22012986, compound

Product 1

HCID 22013056HCID 22013056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.29 g of (RS)-3-(ethoxycarbonylmethyl)-3-((4-methylbenzyl)carbonylamino)indolin-2-one in 10 ml of ethanol was added 2 ml of an aqueous solution of 0.16 g of potassium hydroxide (85%) at room temperature, and the mixture was stirred for 4 hours, followed by concentration. The concentrate was diluted with water, and washed with chloroform. The aqueous layer was adjusted to pH 2 by addition of 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to obtain (RS)-3-(hydroxycarbonyl methyl)-3-((4-methylbenzyl )carbonylamino )indolin-2-one.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with water
  3. washwashed with chloroform
  4. additionThe aqueous layer was adjusted to pH 2 by addition of 2N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-380ed70f57604e039d8fff1077aebc98
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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